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Preparation of certain 2‐ N ‐alkylamino‐and 2‐ N,N ‐dialkylamino‐10‐methylphenothiazines via phenothiazyne
Author(s) -
Biehl E. R.,
Patrizi V.,
Lapis S.,
Reeves P. C.
Publication year - 1974
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570110620
Subject(s) - chemistry , moiety , phenothiazine , acetonitrile , amine gas treating , lithium (medication) , solvent , medicinal chemistry , ammonia , organic chemistry , medicine , pharmacology , endocrinology
The treatment of 2‐chloro‐10‐methylphenothiazine, 1 , with lithium alkylamide/alkylamine or lithium dialkylamide/dialkylamine yields the corresponding 2‐ N ‐alkylamino‐or 2‐ N,N ‐dialkylaminophenothiazines in good yields via phenothiazyne. No significant reduction of 1 to 10‐methylphenothiazine is observed. Yields of amines obtained by this method are considerably higher than those obtained by reacting 1 with sodamide in refluxing amine solvent. Attempts to introduce the ‐CH 2 CN moiety onto the phenothiazine nucleus by treating 1 with sodamide and acetonitrile in liquid ammonia produced only 2‐amino‐10‐methylphenothiazine.